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Simon and Jeanette are the characteristically smart couple who wear glasses and always have a logical explanation for almost anything (almost). Except when Simon takes charge, Jeanette can sometimes be shy and timid and a doormat for Brittany's schemes. Simon and Jeanette share a non-confusing relationship, but are very shy and don't open up about it. Jeanette and Simon, in the series of cartoons, occasionally hold hands and hang out often. Simon is sometimes very defensive of her, and when Jeanette gets clumsy and falls, Simon is usually the one to catch her and help her to her feet. Their actions show that the two care for each other more than friends, but could be embarrassed about it. In Big Dreams, they are portrayed as a married couple and win Nobel Prizes together. In the CGI films series, Alvin and the Chipmunks: Chipwrecked, their shy relationship takes a central role by progressing through a new, temporarily confident, version of Simon.
- In The Chipettes, Simon quickly catches Jeanette when she faints and falls backwards.
- In I Love the Chipmunks Valentine, Simon makes a valentine for Jeanette.
- In The Gang's All Here, Simon helps Jeanette before she falls over.
- In My Fair Chipette, when Jeanette wins the beauty contest, Simon pushes her on stage with a big smile on his face.
- In the Hardees Glass Commercial, Jeanette falls and Simon quickly catches her.
- In Sisters, Brittany is so happy she was invited to lunch that she throws her books at Jeanette causing her to fall. With a worried look, Simon helps Jeanette to her feet.
- In Sweet Smell of Success, when Jeanette and Simon create more perfume and smell it, it seemed as if they would shake hands, but just held each other's hand instead.
- In A Little Worm in the Big Apple, he comforts her by holding her while patting and slightly rubbing her arm.
- In May the Best Chipmunk Win, Simon is excited when he sees Jeanette in their classroom, takes her hand, and have lunch together.
- In The Chipette Story, Simon helps Jeanette take off her shoes.
- In The Chipmunk Adventure, whenever Simon feels "stressed out" with his brothers, he always goes to Jeanette for help. They also dance together during "The Girls of Rock 'n' Roll."
- In Alvin and the Chipmunks Meet the Wolfman, Simon and Jeanette hold hands on the stage when they perform in the school play, and they hold hands and dance several times during the end of the movie.
- In the Hardee's Glass Commercial, Simon and Jeanette dance together.
- In Alvin and the Chipmunks: The Squeakquel, when they meet at school, Simon falls in love with Jeanette. He purrs at her indicating that he has a crush on her.
- In Alvin and the Chipmunks: The Squeakquel, when he is practicing for the concert, he dreamily remarks that Jeanette's glasses were "quite fetching."
- In Alvin and the Chipmunks: The Squeakquel, Simon nervously agrees to help Jeanette unlock the cage she and her sisters are trapped in. This indicates that he is shy talking to her.
- In Alvin and the Chipmunks: The Squeakquel, Simon and Jeanette smile at each other happily when they reunite just before "We Are Family."
- In Alvin and the Chipmunks: Chipwrecked, Simon tells Jeanette on the raft that "Even the most perfect gem cannot compare to your beauty". Jeanette smiles him and Simon smiles back. Simone says just about the same thing earlier, revealing a similarity between Simon and Simone.
- In Alvin and the Chipmunks: Chipwrecked, Simone (Simon's alter ego) dances in the rain with Jeanette, singing with her. He also kisses her hand several times and compliments her.
- In Alvin and the Chipmunks: Chipwrecked, when Jeanette finds one of Simon's sarcastic comments funny, Simon becomes nervous and seems shyly delighted.
- In Alvin and the Chipmunks: Chipwrecked, while The Chipmunks and Chipettes are skating on the ship's deck, Jeanette nearly slips, but Simon catches her by the hand. He holds it for a second before letting go in embarrassment.
- In Alvin and the Chipmunks: Chipwrecked, while on the island, Simon manages to create a fire with his glasses and Jeanette calls it impressive. Simon becomes so flattered that he accidentally burns himself.
- In Alvin and the Chipmunks: Chipwrecked, when Brittany becomes hysterical to the possibility of being stuck on the island forever, Simon protectively puts his arm in front of Jeanette as if to protect her.
- In Alvin and the Chipmunks: Chipwrecked, when Simone is kissing The Chipettes' hands, he is taken by Jeanette before he smiles and kisses her. He also moves really close to her, beautifying her with words.
- Throughout Alvin and the Chipmunks: Chipwrecked, Simone would complement Jeanette, make romantic gestures such as giving her a bracelet, and help her across a dangerous bridge by telling her to look into his eyes.
- In Alvin and the Chipmunks: Chipwrecked, when the side effects wore off, Brittany informs Simon that he had given Jeanette a bracelet and that they had went out on a date, startling him.
- In Alvin and the Chipmunks: Chipwrecked, Simon saves Jeanette from Zoe.
- In My Sister The Weirdo, Simon was the only one who wanted to help Jeanette when she was nervous about public speaking. Simon is also jealous when Jeanette asks for Alvin's help instead of his and is determined to help in any way he can.
- In Saving Simon, Simon looked awestruck when Jeanette complements him while holding his cheeks.
- In Saving Simon, Simon winks at Jeanette.
- In Saving Simon, Simon smiles innocently when Jeanette kisses his cheek.
- In Driving Dave Crazy, Simon looks to Jeanette with softness when he gives her back her spider.
- In Lights Camera Uh Oh, Simon puts his arm around Jeanette's shoulder.
- In Lights Camera Uh Oh, Simon is the first to offer to help Jeanette.
- In She's Got Style, Simon tells Dave to let Jeanette down gently.
- In Secret Admirer, Simon says that Jeanette is especially pretty and he hesitantly says he couldn't care less when Alvin teased him of having a crush on Jeanette.
- In Super Girls, after Alvin told Simon to invent a side clobber gadget because he thought Jeanette side clobbered him, Simon told Alvin to stop spying on poor Jeanette.
- In Super Girls, Simon volunteers at school to help Jeanette with her superhero gadgets.
- In Super Girls, after Simon sees what Jeanette is trying to make, he says that it is ingenious of her.
- In the baseball scene during the introduction of the Alvin and the Chipmunks series, Jeanette is smiling and blinking her eyes at Simon before she turns to pitch the baseball to Brittany.
- In Sploosh, Simon and Jeanette's characters get married.
- In Sploosh, Jeanette and Simon's characters almost kiss.
- In Alvin in Neverland, Tinkerbell (Jeanette) takes John's (Simon) hand and flies off with him.
- In The Greatest Show-Offs on Earth, Jeanette stares at Simon while pushing an elephant named Pinkie.
- In I Love The Chipmunks Valentine Special, Jeanette makes a valentine for Simon. Later, Jeanette dances with Simon, and she blushes when Simon dances with her. Also, when Jeanette has to dress up as Brittany's date and Jeanette calls this a miserable idea, Brittany tells her to relax for she will have plenty of time to be with Simon, implying that Jeanette had wanted to spend her night with him.
- When Jeanette fell in the Hardees Glass Commercial, she stares at him admiringly when he catches her.
- In Mind Over Matterhorn, she is holding on to Simon while waiting on Alvin. Jeanette also leans into Simon's arms to shield her eyes when Alvin climbs down the cliff.
- In The Chipmunks Go to Washington, Jeanette and Simon watch baby eagles in a nest. When Simon looked away after he told her that they should tell the others, she didn't look away. She stared at him for a quick second longer, indicating that she has a crush on him. Later on, Jeanette hugs Simon tightly, and Brittany looks at them with a look that displays she knew her sister had a crush on him.
- In Big Dreams, she comforts Simon, and the two of them are married.
- In Help Wanted: Mommy, when they have to pretend that they're getting along perfectly, they do act like they're having the most fun together. They also walk off with linked arms.
- Jeanette has a picture of Simon in her room.
- In Alvin and the Chipmunks: The Squeakquel, Jeanette expressed great interest and excitement in meeting Simon, much like her sisters were about their counterparts. When Ian told lies about them, saying "And don't even get me started about Simon", Jeanette gasped in shock and disappointment.
- In Alvin and the Chipmunks: The Squeakquel, Jeanette quickly fell in love with him when she met him at the lockers. Her pupils even dilated as she looked at him, indicating that she was caught by surprise and that she was completely ecstatic. When led away, Jeanette further confirmed her crush by saying "That Simon is dreamy."
- In Alvin and the Chipmunks: The Squeakquel, as all six chipmunks prepare for bed, Jeanette and Simon both said warm good nights to each other.
- In Alvin and the Chipmunks: Chipwrecked, after Simone starts falling for Jeanette, she becomes smitten.
- In Alvin and the Chipmunks: Chipwrecked, after Simon describes the shuffleboard as 10% shuffle, 90% board, Jeanette finds it funny, despite his dry sense of humor, causing Simon to blush.
- In Alvin and the Chipmunks: Chipwrecked, after Simon makes a fire with his glasses, Jeanette calls it impressive, but while he's looking at Jeanette, he accidentally burns himself.
- In Saving Simon, Jeanette kisses Simon's cheek after he helps her with her crossword.
- In She's Got Style, Jeanette smiles sweetly at Simon after she takes his cup.
- In Simon the Superb, Jeanette is the only one watching Simon's magic show.
- In Simon the Superb, Jeanette complements Simon's magic show.
- In Lights Camera Uh Oh, Jeanette smiles when Simon offers to help her.
- In Super Girls, after Simon tells Jeanette that it was ingenious of her to make a gadget like that, Jeanette replies saying, "You really think so?"
- Both have very similar signature colors.
- Both wear glasses.
- They are very intelligent.
- In the CGI/live-action versions, they have the darkest tone of fur out of their siblings.
- They are known for their specialties in science.
- They both normally pair up with their overbearing siblings (Alvin and Brittany respectively).
- They are the tallest of the six (Simon a little taller than her).
- They are both usually the ones to carry out Alvin and Brittany's hair-brained schemes.
- They're the shyest about their relationship, where as Brittany and Alvin are open about it but often fight, and Eleanor and Theodore are the most open and loving.
- They are the middle child of their siblings (in the 80s series, their age isn't confirmed for the CGI films and Simon is older than Alvin in ALVINNN!!! and The Chipmunks).
- They are very coward about something dangerous.
- He can easily stand up to Alvin.
- He can almost see better without his glasses than Jeanette can.
- He's not very clumsy. (However, he was voted "Most Likely To Fall Down" in The Brunch Club.)
- He can have a very dry sense of humor.
- He can be very sarcastic.
- He tends to hold grudges, though most eventually disappear.
- He has a low tolerance for trickery or games.
- He's always very uptight about a problem.
- She doesn't stand up for herself easily and is used by Brittany to help carry out schemes.
- Jeanette is helpless without her glasses, possibly suffering from astigmatism.
- Jeanette appears to be more clumsy than Simon.
- Jeanette is more relaxed and is more likely to let herself have fun.
- She is very forgiving.
- She has more patience when it comes to people that do her wrong than Simon does.